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Private Pool
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Parking
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Pool
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View

Discover the Best Resort Vacations
Explore the top resorts, from luxury beachfront escapes to family-friendly all-inclusive resorts and relaxing spa retreats. Whether you’re planning a weekend getaway or an extended vacation, the Charlestown offers world-class resort destinations for every travel style, season, and budget.
Guests
- Hotels
- Villas
- Cabins
- Rentals
- Cottages
- Resorts
- Accommodations
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
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Breakfast
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Parking
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Pool
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Kitchen
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Breakfast
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Parking
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Pool
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Kitchen
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.50 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.05 mi to center
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Balcony/Terrace
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View
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Air Conditioner
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Internet
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Balcony/Terrace
-
View
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Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
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Breakfast
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Parking
-
Pool
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Kitchen
-
Breakfast
-
Parking
-
Pool
-
Kitchen
- Boston
- ·
- Medford Street - The Neck
- 0.13 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Medford Street - The Neck
- 0.16 mi to center
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Parking
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Kitchen
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Air Conditioner
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Internet
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Parking
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Kitchen
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Air Conditioner
-
Internet
- Boston
- ·
- Charlestown
- 0.59 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.28 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.50 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.05 mi to center
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Balcony/Terrace
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View
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Air Conditioner
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Internet
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Balcony/Terrace
-
View
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Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
-
Breakfast
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Parking
-
Pool
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Kitchen
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Breakfast
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Parking
-
Pool
-
Kitchen
- Boston
- ·
- Medford Street - The Neck
- 0.13 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Medford Street - The Neck
- 0.16 mi to center
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Parking
-
Kitchen
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Air Conditioner
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Internet
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
- Boston
- ·
- Charlestown
- 0.59 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.28 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.50 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.05 mi to center
-
Balcony/Terrace
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View
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Air Conditioner
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Internet
-
Balcony/Terrace
-
View
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Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
-
Breakfast
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Parking
-
Pool
-
Kitchen
-
Breakfast
-
Parking
-
Pool
-
Kitchen
- Boston
- ·
- Medford Street - The Neck
- 0.13 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
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Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Medford Street - The Neck
- 0.16 mi to center
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Parking
-
Kitchen
-
Air Conditioner
-
Internet
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
- Boston
- ·
- Charlestown
- 0.59 mi to center
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.28 mi to center
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
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Internet
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.50 mi to center
-
Parking
-
Balcony/Terrace
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Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.05 mi to center
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Balcony/Terrace
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View
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Air Conditioner
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Internet
-
Balcony/Terrace
-
View
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Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
-
Breakfast
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Parking
-
Pool
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Kitchen
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Breakfast
-
Parking
-
Pool
-
Kitchen
- Boston
- ·
- Medford Street - The Neck
- 0.13 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
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Air Conditioner
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
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Air Conditioner
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Medford Street - The Neck
- 0.16 mi to center
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Parking
-
Kitchen
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Air Conditioner
-
Internet
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
- Boston
- ·
- Charlestown
- 0.59 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.28 mi to center
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.50 mi to center
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.05 mi to center
-
Balcony/Terrace
-
View
-
Air Conditioner
-
Internet
-
Balcony/Terrace
-
View
-
Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
-
Breakfast
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Parking
-
Pool
-
Kitchen
-
Breakfast
-
Parking
-
Pool
-
Kitchen
- Boston
- ·
- Medford Street - The Neck
- 0.13 mi to center
-
Parking
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Balcony/Terrace
-
Kitchen
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Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
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Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Medford Street - The Neck
- 0.16 mi to center
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Parking
-
Kitchen
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Air Conditioner
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Internet
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
- Boston
- ·
- Charlestown
- 0.59 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.28 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
-
Kitchen
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Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.50 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
-
Kitchen
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Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.05 mi to center
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Balcony/Terrace
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View
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Air Conditioner
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Internet
-
Balcony/Terrace
-
View
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Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
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Breakfast
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Parking
-
Pool
-
Kitchen
-
Breakfast
-
Parking
-
Pool
-
Kitchen
- Boston
- ·
- Medford Street - The Neck
- 0.13 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Medford Street - The Neck
- 0.16 mi to center
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Parking
-
Kitchen
-
Air Conditioner
-
Internet
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
- Boston
- ·
- Charlestown
- 0.59 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.28 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
Find the Perfect Resort Vacation in the Charlestown
What makes our resorts stand out?
Verified Properties
Every vacation home shown on Resort Vacation comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Popular Resort Destinations in the Charlestown
What are the Top Resort Locations Across the Charlestown?
Discover resorts in the most sought-after travel destinations nationwide:
Medford Street - The Neck
Medford Street - The Neck VACATION RENTALSJohn Harvard Mall
John Harvard Mall VACATION RENTALSGreat House Site
Great House Site VACATION RENTALSRound Corner House
Round Corner House VACATION RENTALSWinthrop Park
Winthrop Park VACATION RENTALSEngine Company 50
Engine Company 50 VACATION RENTALSNational Park Service Visitor Center
National Park Service Visitor Center VACATION RENTALSBreed's Hill
Breed's Hill VACATION RENTALSStatue of General Warren
Statue of General Warren VACATION RENTALSBoston National Historical Park
Boston National Historical Park VACATION RENTALSCharlestown Navy Yard Visitor Center
Charlestown Navy Yard Visitor Center VACATION RENTALSThompson Square - Bunker Hill
Thompson Square - Bunker Hill VACATION RENTALSHow to Reserve Your Resorts Vacation Accommodation?
Booking Made Simple
Resorts Vacations connects travelers with verified resort stays from trusted partners across the Charlestown. Once you find the perfect resort, you’ll be seamlessly guided to our partner’s secure booking platform to complete your reservation with confidence.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Common Resort Vacation Amenities in the Charlestown
What Amenities Can You Expect When Booking with Resorts Vacations?
Resorts Vacations offers carefully selected resort stays across the Charlestown, designed for comfort, convenience, and memorable experiences.
Indoor Amenities
Spacious guest rooms and suites
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Places to Stay with Resorts Vacations
Looking for the perfect resort vacation in the Charlestown? Discover a curated collection of resort stays offering comfort, convenience, and unforgettable experiences in top destinations nationwide. Whether you’re searching for a beachfront resort, a family-friendly escape, or a luxury retreat, Resorts Vacations makes it easy to explore and compare verified resort options for your next getaway.
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.28 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
- Boston
- ·
- Charlestown
- 0.59 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.05 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
- Boston
- ·
- Medford Street - The Neck
- 0.30 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.06 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.34 mi to center
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
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Hot Tub
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Parking
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Pool
-
Balcony/Terrace
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.48 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.05 mi to center
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Balcony/Terrace
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View
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Air Conditioner
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Internet
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Balcony/Terrace
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View
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Air Conditioner
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Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.25 mi to center
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Parking
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Kitchen
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Air Conditioner
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Internet
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Parking
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Kitchen
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Air Conditioner
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Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.45 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Boston
- ·
- Charlestown
- 0.59 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.52 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
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View
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Kitchen
Resorts Vacations FAQs
Which vacation homes in Charlestown are best for families?
If you are looking for a family-friendly vacation home in Charlestown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Charlestown:
How many vacation rentals are available in Charlestown?
Currently, the total number of properties listed in 2026 is over 61 in the Charlestown area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Charlestown.
More Resorts Vacations to Explore
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.25 mi to center
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Parking
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Kitchen
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Air Conditioner
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Internet
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Parking
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Kitchen
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Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.43 mi to center
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Parking
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Kitchen
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Air Conditioner
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Internet
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Parking
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Kitchen
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Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.26 mi to center
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Kitchen
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Air Conditioner
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Internet
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Laundry
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Kitchen
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Air Conditioner
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Internet
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Laundry
- Boston
- ·
- Medford Street - The Neck
- 0.36 mi to center
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Air Conditioner
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Internet
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Security/Safety
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Air Conditioner
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Internet
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Security/Safety
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.33 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.52 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
-
View
-
Kitchen
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.05 mi to center
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Balcony/Terrace
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View
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Air Conditioner
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Internet
-
Balcony/Terrace
-
View
-
Air Conditioner
-
Internet
- Boston
- ·
- Medford Street - The Neck
- 0.30 mi to center
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Breakfast
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Parking
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View
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Air Conditioner
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Breakfast
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Parking
-
View
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Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.44 mi to center
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Pool
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Kitchen
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Air Conditioner
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Internet
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Pool
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Kitchen
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Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.28 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Balcony/Terrace
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Kitchen
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Air Conditioner
-
Internet
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.50 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Boston
- ·
- Thompson Square - Bunker Hill
- 0.06 mi to center
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Parking
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Air Conditioner
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Internet
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Child Friendly
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Parking
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Air Conditioner
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Internet
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Child Friendly